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WO2018135626A1 - Composition contenant une poudre, procédé de production associé et préparation cosmétique - Google Patents

Composition contenant une poudre, procédé de production associé et préparation cosmétique Download PDF

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Publication number
WO2018135626A1
WO2018135626A1 PCT/JP2018/001618 JP2018001618W WO2018135626A1 WO 2018135626 A1 WO2018135626 A1 WO 2018135626A1 JP 2018001618 W JP2018001618 W JP 2018001618W WO 2018135626 A1 WO2018135626 A1 WO 2018135626A1
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Prior art keywords
powder
solvent
charge
mass
composition according
Prior art date
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Ceased
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PCT/JP2018/001618
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English (en)
Japanese (ja)
Inventor
那須昭夫
佐藤根大士
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Shiseido Co Ltd
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Shiseido Co Ltd
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Filing date
Publication date
Application filed by Shiseido Co Ltd filed Critical Shiseido Co Ltd
Priority to BR112019014612-1A priority Critical patent/BR112019014612A2/pt
Priority to EP18741641.7A priority patent/EP3572467A4/fr
Priority to US16/477,659 priority patent/US20190358131A1/en
Priority to JP2018562453A priority patent/JP6909240B2/ja
Priority to KR1020197020327A priority patent/KR102241317B1/ko
Priority to RU2019123826A priority patent/RU2761628C2/ru
Priority to CN201880008090.5A priority patent/CN110177842B/zh
Publication of WO2018135626A1 publication Critical patent/WO2018135626A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/044—Suspensions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216—Solid or semisolid forms
    • A61K8/022—Powders; Compacted Powders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/24—Phosphorous; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/413—Nanosized, i.e. having sizes below 100 nm
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5424—Polymers characterized by specific structures/properties characterized by the charge anionic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/61—Surface treated
    • A61K2800/614—By macromolecular compounds

Definitions

  • the present disclosure relates to a liquid composition having a powder in a solvent and a method for producing the same.
  • the present disclosure also relates to a cosmetic having the composition.
  • Slurry products in which solid particles are dispersed in a solvent are used in a wide range of fields such as foods, paints, cosmetics, inks and ceramics.
  • a technique for improving the dispersibility of particles has been developed (see, for example, Patent Document 1 and Non-Patent Document 1).
  • the organic-inorganic composite particle dispersion described in Patent Document 1 is obtained by converting organic-inorganic composite particles into oils, waxes, hydrocarbons, fatty acids, alcohols, alkyl glyceryl ethers, esters, polyhydric alcohols, saccharides.
  • the organic-inorganic composite particles are dispersed in a solvent selected from silicone oil, crosslinked silicone gel, and fluorine oil or a mixed solvent thereof in the range of 0.001 to 50% by weight.
  • Organic organic cosmetics in which polymer gel molecules derived from natural products having an anionic functional group and one or more hydroxyl groups in the molecule are electrostatically bonded to the surface of the inorganic oxide particles. Inorganic composite particles.
  • Non-Patent Document 1 a slurry in which alumina particles are dispersed in ion-exchanged water is prepared using ammonium polycarboxylate as a polymer dispersant.
  • the polymer chain adsorbed on the particle surface is contracted in a coil shape.
  • the above-mentioned slurry product is usually prepared so that the ratio of the solvent and the powder is optimal.
  • there is a density difference between the solvent and the powder so that if left standing, the powder settles and forms a solidified deposited layer, and there is a problem that the function as a product is lost. .
  • a method is sometimes used in which solid particles are crushed to several tens of nanometers or less, so that the sedimentation rate is extremely reduced and the solution is solved kinetically.
  • the sedimentation rate is extremely slow, solidification of the powder during standing for a long time has not been completely prevented. For this reason, there is a need for an inexpensive, simple and radical solution that facilitates redispersion.
  • Non-Patent Document 1 since the polymer is not sufficiently elongated, the polymer is cross-linked between the non-adsorbed surfaces of the particles to form aggregates. This causes the problem of powder solidification as described above. Also in the organic-inorganic composite particle dispersion described in Patent Document 1, it is considered that the same aggregation as the slurry described in Non-Patent Document 1 occurs. If such agglomeration occurs, redispersion of the powder becomes difficult.
  • a solvent a powder present in the solvent and having a first charge on the surface, and an ionic polymer having a second charge opposite to the first charge, And a multivalent ion having a first charge.
  • the powder and the ionic polymer are electrostatically and / or ionically bound.
  • the ionic polymer and the multivalent ion are electrostatically and / or ionically bonded.
  • a composition including a powder having a first charge on the surface, polyacrylate ions and / or hexametaphosphate ions, and magnesium ions.
  • the content of the powder is 10% by mass to 50% by mass with respect to the mass of the composition.
  • the content of the polymer electrolyte that is the source of polyacrylate ions and / or hexametaphosphate ions is 0.005 parts by mass to 0.5 parts by mass with respect to 1 part by mass of the powder.
  • the content of the salt serving as the source of magnesium ions is 0.05 to 5 parts by mass with respect to 1 part by mass of the polymer electrolyte.
  • a cosmetic containing the composition according to the first viewpoint and / or the second viewpoint is provided.
  • a first addition step of adding a powder having a surface having a first charge in a solvent to a solvent containing water, and a first step opposite to the first charge in the solvent A second addition step in which a polymer electrolyte that ionizes the ionic polymer having two charges is added to the solvent, and after the first addition step and the second addition step, And a third addition step in which a salt that generates a valent ion is added to a solvent.
  • a first addition step of adding a powder having a surface having a first charge in a solvent to a solvent containing water, and a first step opposite to the first charge in the solvent A second addition step of adding a polymer electrolyte that ionizes the ionic polymer having two charges to the solvent, a charging step of charging the surface of the powder to the first charge in the solvent, and after the charging step, And a third addition step of adding, to the solvent, a salt that generates a multivalent ion having a first charge in the solvent.
  • the powder in the composition of the present disclosure has a low sedimentation rate. Even if the powder settles upon standing, the powder can be easily redispersed by gently shaking the container. That is, the composition of the present disclosure has high stability during storage and is easy to flow and use during use.
  • the powder constitutes a soft agglomerate through an ionic polymer and multivalent ions.
  • the average particle size of the composite in which the ionic polymer adheres to the powder is 200 nm to 800 nm.
  • the first charge is a positive charge.
  • the second charge is a negative charge.
  • the powder is zinc oxide.
  • the content of the powder is 10% by mass to 50% by mass with respect to the mass of the composition.
  • the average particle diameter of the powder is 10 nm to 200 nm.
  • the ionic polymer has an anionic functional group.
  • the ionic polymer is a polyacrylate ion and / or a hexametaphosphate ion.
  • the content of the polymer electrolyte that is the source of the ionic polymer is 0.005 parts by mass to 0.5 parts by mass with respect to 1 part by mass of the powder.
  • the multivalent ions are magnesium ions and / or calcium ions.
  • the content of the salt that is the source of the polyvalent ions is 0.05 to 5 parts by mass with respect to 1 part by mass of the polymer electrolyte that is the source of the ionic polymer. is there.
  • the solvent includes water.
  • the powder is zinc oxide.
  • the pH of the solvent is adjusted in the charging step.
  • a charging agent that charges the surface of the powder to the first charge is added to the solvent.
  • the charging agent is a cationic polymer.
  • the method for producing the composition further includes a relaxation step for relaxing the contraction of the polymer chain of the ionic polymer.
  • pressure is applied to the solvent in the relaxation step.
  • the powder is zinc oxide.
  • the average particle size of the powder is 10 nm to 200 nm.
  • the polymer electrolyte is polyacrylate and / or hexametaphosphate.
  • the salt is a magnesium salt and / or a calcium salt.
  • POE is an abbreviation for polyoxyethylene and POP is an abbreviation for polyoxypropylene.
  • the number in parentheses after POE or POP represents the average added mole number of POE group or POP group in the compound.
  • composition of the present disclosure has a solvent, a powder present in the solvent, an ionic polymer (polymer ion generated from the ionic polymer), and a multivalent ion.
  • the solvent is preferably an ionic polymer and a metal salt that dissociates multivalent ions as a soluble liquid.
  • the solvent is preferably a polar solvent so that the ionic substance can be dissolved, and more preferably an aqueous solvent.
  • an aqueous solvent water, alcohol, or a mixture thereof can be mentioned, for example.
  • lower alcohols examples include ethanol, propanol, isopropanol, isobutyl alcohol, t-butyl alcohol and the like.
  • polyhydric alcohol examples include divalent alcohols (for example, ethylene glycol, propylene glycol, trimethylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, tetramethylene glycol, 2,3-butylene glycol, Pentamethylene glycol, 2-butene-1,4-diol, hexylene glycol, octylene glycol, etc.); trivalent alcohol (eg, glycerin, trimethylolpropane, etc.); tetravalent alcohol (eg, 1, 2, 6) Pentaerythritol, such as hexanetriol, etc .; pentavalent alcohol (eg, xylitol, etc.); hexavalent alcohol (eg, sorbitol, mannitol, etc.); polyhydric alcohol polymer (eg, diethylene glycol, dipropylene glycol, Ethylene glycol, polypropylene glycol, tetraethylene glycol,
  • the solvent content can be the remainder of the other components.
  • the solvent can be 40% by mass or more, 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, or 90% by mass or more with respect to the mass of the composition.
  • a solvent can be 95 mass% or less, 90 mass% or less, 80 mass% or less, 70 mass% or less, or 60 mass% or less with respect to the mass of a composition.
  • the composition can contain a powder.
  • the composition may contain a plurality of types of particles.
  • the powder is preferably insoluble in a solvent.
  • the powder is first charged on the surface in the solvent.
  • the first charge may be a charge charged by a charging agent.
  • the first charge may be a positive charge or a negative charge.
  • Analysis / evaluation of having the first charge can be performed by measuring an isoelectric point, measuring pH, or the like.
  • Examples of the powder having a positive surface charge include zinc oxide, alumina, and titanium oxide.
  • Examples of the powder having a negative surface charge include silica.
  • the average particle diameter of the powder is preferably 5 nm or more, and more preferably 10 nm or more. If it is less than 5 nm, handling becomes difficult.
  • the average particle size of the powder can be 200 nm or less or 100 nm or less.
  • the average particle diameter of the powder can be measured according to the dynamic light scattering method.
  • the powder content can be 5% by mass or more, 10% by mass or more, or 20% by mass or more with respect to the mass of the composition. Moreover, the content rate of a powder can be 50 mass% or less or 40 mass% or less with respect to the mass of a composition.
  • the powder examples include inorganic powders (for example, talc, kaolin, mica, sericite (sericite), muscovite, phlogopite, synthetic mica, red mica, biotite, lithia mica, calcined mica, calcined talc, permiculite, Magnesium carbonate, calcium carbonate, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, strontium silicate, metal tungstate, magnesium, silica, zeolite, glass, barium sulfate, calcined calcium sulfate (baked gypsum), Calcium phosphate, fluorapatite, hydroxyapatite, ceramic powder, metal soap (eg, zinc myristate, calcium palmitate, aluminum stearate), boron nitride, etc .; Organic powder (eg, polyamide resin powder (nylon powder), polyethylene powder Polymethyl methacrylate powder, polystyrene powder, copo
  • the composition of the present disclosure contains at least one ionic polymer.
  • the ionic polymer may be a polymer that becomes an ion in a solvent.
  • the sign of the ionic polymer is preferably determined according to the charge of the powder.
  • One ionic polymer can have one or more ionic functional groups.
  • the valence of the ionic polymer may be monovalent or multivalent.
  • the ionic polymer can be added in the form of a polymer electrolyte.
  • the polyelectrolyte can be in acid or base form.
  • the ionic polymer has a second charge opposite to the first charge due to ionization in the solvent.
  • the ionic polymer has one or more ionic functional groups that are ionized in a solvent and have a second charge in the constituent component or substituent of the polymer chain. It is preferable that the valence of one functional group is lower than the valence of the multivalent ion. More preferably, the valence of one functional group is monovalent in order to electrostatically and / or ionically bond a plurality of ionic polymers to the multivalent ion.
  • Examples of the anionic functional group of the ionic polymer include carboxylic acid, sulfurous acid, sulfuric acid, acrylic acid, and salts thereof.
  • Examples of the cationic functional group of the ionic polymer include amine salts and imine salts.
  • anionic ionic polymer examples include polyacrylate, hexametaphosphate, polycarboxylic acid (polymer of carboxylic acid monomer), and the like.
  • cationic ionic polymer examples include a polymer having a quaternary ammonium group.
  • the molecular weight of the ionic polymer is preferably 3,000 or more, more preferably 5,000 or more, and further preferably 6,000 or more. Soft aggregation cannot be formed as it is less than 3,000.
  • the molecular weight of the ionic polymer is preferably 15,000 or less, more preferably 12,000 or less, and even more preferably 10,000 or less. If it exceeds 15,000, stickiness will appear as a feeling of use.
  • the content of the salt (polymer electrolyte) serving as the basis of the ionic polymer in the composition is preferably 0.005 parts by mass or more, and 0.008 parts by mass or more with respect to 1 part by mass of the powder. More preferably, it is more preferably 0.01 parts by mass or more, more preferably 0.015 parts by mass or more, and further preferably 0.02 parts by mass or more. It is because the dispersibility of powder will fall that the content rate of a polymer electrolyte is less than 0.005 mass part.
  • the content of the salt (polymer electrolyte) serving as the basis of the ionic polymer is preferably 0.5 parts by mass or less and more preferably 0.4 parts by mass or less with respect to 1 part by mass of the powder. Preferably, the amount is 0.3 parts by mass or less. If the content of the polymer electrolyte exceeds 0.5 parts by mass, the use feeling will be adversely affected.
  • Multivalent ions are ions having a first charge in a solvent.
  • the multivalent ion is preferably an ion having a valence of 2 or more.
  • the multivalent ion can be, for example, a metal ion.
  • the polyvalent ions as cations include metal ions such as aluminum, magnesium, calcium, manganese, barium, nickel, iron, zinc, copper, bismuth, tin, and silver.
  • the polyvalent ion as an anion include sulfate ion and carbonate ion. Of these, magnesium ions and calcium ions are particularly preferable from the viewpoint of safety.
  • the multivalent ion when the multivalent ion is a metal ion, the multivalent ion can be added in the form of a metal salt.
  • the metal salt only needs to be ionized (dissolved) in a solvent.
  • the metal salt include metal salts such as chloride salts, hydroxide salts, nitrates, sulfates, phosphates, acetates, carbonates, and the like. These metal salts can be used alone or in combination of two or more.
  • the content of the salt serving as the basis of the polyvalent ions is preferably 0.05 parts by mass or more with respect to 1 part by mass of the polymer electrolyte from which the ionic polymer is based. More preferably, it is 08 mass parts or more, More preferably, it is 0.1 mass part or more, More preferably, it is 0.15 mass part or more, More preferably, it is 0.2 mass part or more.
  • the content of the salt serving as the basis of the multivalent ions is less than 0.05 parts by mass, the effect of increasing the redispersibility cannot be obtained.
  • the content of the salt serving as the basis of the polyvalent ions is preferably 5 parts by mass or less, and more preferably 3 parts by mass or less with respect to 1 part by mass of the polymer electrolyte that is the source of the ionic polymer. Preferably, it is more preferably 2 parts by mass or less. If the content of multivalent ions exceeds 5 parts by mass, stickiness will appear. Increasing the content of multivalent ions can increase the viscosity of the composition.
  • the composition of the present disclosure may contain a charging agent (charging agent) that charges the surface of the powder to the first charge when the powder is not charged in the solvent.
  • a charging agent for charging the surface of the powder to a positive charge for example, a cationic polymer such as polyethyleneimine can be used.
  • a charging agent for charging the surface of the powder to a negative charge for example, an anionic polymer such as polyacrylate can be used.
  • composition of the present disclosure has other components such as an ester, an anionic surfactant, a cationic surfactant, an amphoteric surfactant, a nonionic surfactant, a humectant, an aqueous solution, as long as the effects of the present disclosure are not impaired.
  • Polymers, thickeners, film agents, UV absorbers, sequestering agents, amino acids, organic amines, polymer emulsions, pH adjusters, skin nutrients, vitamins, antioxidants, antioxidant aids, fragrances, Water or the like can be appropriately contained as necessary.
  • Anionic surfactants include, for example, fatty acid soaps (eg, sodium laurate, sodium palmitate, etc.); higher alkyl sulfates (eg, sodium lauryl sulfate, potassium lauryl sulfate, etc.); alkyl ether sulfates (eg, POE-lauryl sulfate triethanolamine, POE-sodium lauryl sulfate, etc.); N-acyl sarcosine acid (eg, sodium lauroyl sarcosine, etc.); higher fatty acid amide sulfonate (eg, sodium N-myristoyl-N-methyl taurate, palm Oil fatty acid methyl tauride sodium, lauryl methyl tauride sodium, etc.); phosphate ester salts (POE-oleyl ether sodium phosphate, POE-stearyl ether phosphate, etc.); sulfosuccinate ( For example, sodium di-2-eth
  • Examples of the cationic surfactant include alkyltrimethylammonium salts (eg, stearyltrimethylammonium chloride, lauryltrimethylammonium chloride, etc.); alkylpyridinium salts (eg, cetylpyridinium chloride, etc.); distearyldimethylammonium dialkyldimethylammonium chloride; Poly (N, N′-dimethyl-3,5-methylenepiperidinium chloride); alkyl quaternary ammonium salt; alkyldimethylbenzylammonium salt; alkylisoquinolinium salt; dialkyl morpholinium salt; POE-alkylamine; Examples include alkylamine salts; polyamine fatty acid derivatives; amyl alcohol fatty acid derivatives; benzalkonium chloride; benzethonium chloride and the like.
  • alkyltrimethylammonium salts eg, stearyltrimethylammonium chloride, lauryltrimethyl
  • amphoteric surfactants examples include imidazoline-based amphoteric surfactants (eg, 2-undecyl-N, N, N- (hydroxyethylcarboxymethyl) -2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide). Side-1-carboxyethyloxy disodium salt, etc.); betaine surfactants (for example, 2-heptadecyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, lauryldimethylaminoacetic acid betaine, alkylbetaine, amide betaine) , Sulfobetaine, etc.).
  • imidazoline-based amphoteric surfactants eg, 2-undecyl-N, N, N- (hydroxyethylcarboxymethyl) -2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide).
  • lipophilic nonionic surfactant examples include sorbitan fatty acid esters (for example, sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan sesquioleate, sorbitan Trioleate, penta-2-ethylhexyl diglycerol sorbitan, tetra-2-ethylhexyl diglycerol sorbitan, etc.); glycerin polyglycerin fatty acid (eg mono cottonseed oil fatty acid glycerin, monoerucic acid glycerin, sesquioleate glycerin, glyceryl monostearate) , ⁇ , ⁇ '-oleic acid pyroglutamate glycerin, monostearate glycerin malate, etc.); propylene glycol fatty acid esters (eg mono
  • hydrophilic nonionic surfactants include POE-sorbitan fatty acid esters (eg, POE-sorbitan monooleate, POE-sorbitan monostearate, POE-sorbitan monooleate, POE-sorbitan tetraoleate, etc.); POE-sorbite fatty acid ester (eg POE-sorbite monolaurate, POE-sorbite monooleate, POE-sorbite pentaoleate, POE-sorbite monostearate, etc.); POE-glycerin fatty acid ester (eg POE-glycerin monoester) POE-monooleate such as stearate, POE-glycerin monoisostearate, POE-glycerin triisostearate, etc .; POE-fatty acid esters (eg POE-distearate, POE) Monodiolates, ethylene glycol distearate, etc.); POE-alkyl
  • humectant examples include polyethylene glycol, propylene glycol, glycerin, 1,3-butylene glycol, xylitol, sorbitol, maltitol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronic acid, atelocollagen, cholesteryl-12-hydroxystearate Sodium lactate, bile salt, dl-pyrrolidone carboxylate, alkylene oxide derivative, short-chain soluble collagen, diglycerin (EO) PO adduct, Izayoi rose extract, yarrow extract, merirot extract and the like.
  • EO diglycerin
  • natural water-soluble polymers include plant-based polymers (for example, gum arabic, tragacanth gum, galactan, guar gum, carob gum, caraya gum, carrageenan, pectin, agar, quince seed (malmello), alge colloid (guckweed extract), starch (Rice, corn, potato, wheat), glycyrrhizic acid); microbial polymer (eg, xanthan gum, dextran, succinoglucan, pullulan, etc.); animal polymer (eg, collagen, casein, albumin, gelatin, etc.), etc. Is mentioned.
  • plant-based polymers for example, gum arabic, tragacanth gum, galactan, guar gum, carob gum, caraya gum, carrageenan, pectin, agar, quince seed (malmello), alge colloid (guckweed extract), starch (Rice, corn, potato, wheat), glycyrrhizic acid);
  • Semi-synthetic water-soluble polymers include, for example, starch polymers (eg, carboxymethyl starch, methylhydroxypropyl starch, etc.); cellulose polymers (methylcellulose, ethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, sodium cellulose sulfate) Hydroxypropylcellulose, carboxymethylcellulose, sodium carboxymethylcellulose, crystalline cellulose, cellulose powder and the like); alginic acid polymers (for example, sodium alginate, propylene glycol alginate, etc.) and the like.
  • starch polymers eg, carboxymethyl starch, methylhydroxypropyl starch, etc.
  • cellulose polymers methylcellulose, ethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, sodium cellulose sulfate Hydroxypropylcellulose, carboxymethylcellulose, sodium carboxymethylcellulose, crystalline cellulose, cellulose powder and the like
  • alginic acid polymers for example, sodium
  • Synthetic water-soluble polymers include, for example, vinyl polymers (eg, polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, carboxyvinyl polymer); polyoxyethylene polymers (eg, polyethylene glycol 20,000, 40). , 000, 60,0000 polyoxyethylene polyoxypropylene copolymer, etc.); acrylic polymers (for example, sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.); polyethyleneimine; cationic polymers and the like.
  • vinyl polymers eg, polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, carboxyvinyl polymer
  • polyoxyethylene polymers eg, polyethylene glycol 20,000, 40. , 000, 60,0000 polyoxyethylene polyoxypropylene copolymer, etc.
  • acrylic polymers for example, sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.
  • polyethyleneimine
  • thickener examples include gum arabic, carrageenan, caraya gum, gum tragacanth, carob gum, quince seed (malmello), casein, dextrin, gelatin, sodium pectate, sodium alginate, methylcellulose, ethylcellulose, CMC, hydroxyethylcellulose, hydroxypropyl Cellulose, PVA, PVM, PVP, sodium polyacrylate, carboxyvinyl polymer, locust bean gum, guar gum, tamarind gum, cellulose dialkyldimethylammonium sulfate, xanthan gum, magnesium aluminum silicate, bentonite, hectorite, silicate A1Mg (bee gum), Examples thereof include laponite and silicic anhydride.
  • the coating agent examples include an anionic coating agent (for example, (meth) acrylic acid / (meth) acrylic acid ester copolymer, methyl vinyl ether / maleic anhydride polymer), and a cationic coating agent (for example, cation Cellulose, dimethyldiallylammonium chloride polymer, dimethyldiallylammonium chloride / acrylamide copolymer, etc.), nonionic coating agent (eg, polyvinyl alcohol, polyvinylpyrrolidone, polyvinyl acetate, polyacrylate copolymer, (meth) Acrylamide, polymer silicone, silicone resin, trimethylsiloxysilicate, etc.).
  • an anionic coating agent for example, (meth) acrylic acid / (meth) acrylic acid ester copolymer, methyl vinyl ether / maleic anhydride polymer
  • a cationic coating agent for example, cation Cellulose, dimethyldiallylammonium chloride polymer, dimethyldially
  • ultraviolet absorber examples include benzoic acid-based ultraviolet absorbers (for example, paraaminobenzoic acid (hereinafter abbreviated as PABA), PABA monoglycerin ester, N, N-dipropoxy PABA ethyl ester, N, N-diethoxy PABA ethyl ester.
  • PABA paraaminobenzoic acid
  • PABA monoglycerin ester N, N-dipropoxy PABA ethyl ester
  • N, N-diethoxy PABA ethyl ester examples include benzoic acid-based ultraviolet absorbers (for example, paraaminobenzoic acid (hereinafter abbreviated as PABA), PABA monoglycerin ester, N, N-dipropoxy PABA ethyl ester, N, N-diethoxy PABA ethyl ester.
  • PABA paraaminobenzoic acid
  • Salicylic acid-based ultraviolet absorbers eg, amyl salicylate, menthyl salicylate, homomenthyl salicylate, octyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanol phenyl salicylate
  • cinnamic acid-based ultraviolet absorbers For example, octylmethoxycinnamate, ethyl-4-isopropylcinnamate, methyl-2,5-diisopropylcinnamate, ethyl-2,4-diisopropylcinnamate, methyl-2,4-diisopropylcinnamate, propyl-p-methoxy Cinnamate, isopropyl-
  • sequestering agent examples include 1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, disodium edetate, trisodium edetate, and tetrasodium edetate.
  • amino acids examples include neutral amino acids (eg, threonine, cysteine, etc.); basic amino acids (eg, hydroxylysine, etc.), and the like.
  • amino acid derivatives include acyl sarcosine sodium (lauroyl sarcosine sodium), acyl glutamate, acyl ⁇ -alanine sodium, glutathione, and pyrrolidone carboxylic acid.
  • organic amines examples include monoethanolamine, diethanolamine, triethanolamine, morpholine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, and 2-amino-2-methyl-1-propanol. Is mentioned.
  • polymer emulsion examples include acrylic resin emulsion, polyethyl acrylate emulsion, acrylic resin liquid, polyacryl alkyl ester emulsion, polyvinyl acetate resin emulsion, natural rubber latex, and the like.
  • pH adjuster examples include buffers such as lactic acid-sodium lactate, citric acid-sodium citrate, and succinic acid-sodium succinate.
  • vitamins examples include vitamins A, B1, B2, B6, C, E and derivatives thereof, pantothenic acid and derivatives thereof, and biotin.
  • antioxidants examples include tocopherols, dibutylhydroxytoluene, butylhydroxyanisole, gallic acid esters and the like.
  • antioxidant assistant examples include phosphoric acid, citric acid, ascorbic acid, maleic acid, malonic acid, succinic acid, fumaric acid, kephalin, hexametaphosphate, phytic acid, ethylenediaminetetraacetic acid and the like.
  • ingredients that can be blended include, for example, preservatives (ethyl paraben, butyl paraben, chlorphenesin, phenoxyethanol, etc.); anti-inflammatory agents (eg, glycyrrhizic acid derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.
  • preservatives ethyl paraben, butyl paraben, chlorphenesin, phenoxyethanol, etc.
  • anti-inflammatory agents eg, glycyrrhizic acid derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.
  • Whitening agent eg, placenta extract, saxifrage extract, arbutin, etc.
  • various extracts eg, buckwheat, auren, shikon, peonies, assembly, birch, sage, loquat, carrot, aloe, mallow, iris, grape , Yokuinin, Loofah, Lily, Saffron, Senkyu, Pepper, Hypericum, Onionis, Garlic, Pepper, Chimpi, Toki, Seaweed, etc.
  • Activator eg, Royal Jelly, Photosensitive Element, Cholesterol Derivative, etc.
  • composition of the present disclosure includes caffeine, tannin, verapamil, tranexamic acid and derivatives thereof, various herbal extracts such as licorice, karin, and yew, etc., tocopherol acetate, glycyrrhizic acid, glycyrrhizic acid and derivatives or salts thereof, etc.
  • Drugs, vitamin C, magnesium ascorbate phosphate, glucoside ascorbate, whitening agents such as arbutin and kojic acid, amino acids such as arginine and lysine, and derivatives thereof can also be contained as appropriate.
  • FIG. 1 the schematic diagram which shows the dispersion form in the composition of this indication is shown.
  • the surface of the powder has a first charge (positive charge in FIG. 1).
  • the ionic polymer is ionized in the solvent and has a second charge (negative charge in FIG. 1).
  • the polymer ions are considered to be gathered near the surface of the powder so as to maintain electrical neutrality.
  • the solvent it is considered to be electrostatically and / or ionically bound to the surface of the powder.
  • the ionic polymer is considered to be attached or adsorbed on the surface of the powder. Thereby, it is considered that the powder and the ionic polymer form a complex.
  • a plurality of ionic polymers are bonded or attached to one primary particle and / or secondary particle of the powder.
  • the polymer chain of the ionic polymer does not shrink around the powder and extends outward from the powder.
  • the average particle size of the composite can be 200 nm or more.
  • the average particle size of the composite can be 800 nm or less.
  • the average particle diameter of the composite can be measured according to the dynamic light scattering method.
  • the polydispersity index (PDI (Polydispersity Index) value) of the composite is preferably 0.2 or less.
  • the polydispersity index can be obtained by calculation from the particle size distribution measured according to the dynamic light scattering method.
  • the multivalent ions are electrostatically and / or ionicly mixed with the ionic polymer having the second charge in the solvent. It is thought that it is combined with.
  • the multivalent ions are considered to be electrostatically and / or ionically bound to a plurality of ionic polymers adsorbed on different powders. Thereby, it is thought that the multivalent ion has a structure that crosslinks the ionic polymer or the composite. That is, it is considered that the powder, the ionic polymer, and the multivalent ions form a network form by weak ionic bonds or ions and / or electrostatic interactions.
  • the powder is softly agglomerated through the ionic polymer and the multivalent ions. And it is thought that the network form and / or soft aggregation suppresses the sedimentation of the powder and suppresses the solidification even when the powder settles. In addition, since the mesh form and / or soft aggregation can be easily decomposed by an external force, it is considered that the reflow and redispersion of the powder after standing are facilitated by an external force such as shaking.
  • the sedimentation of the powder can be suppressed. Moreover, even if it is left still and the powder settles, solidification of the powder can be suppressed.
  • the powder can be easily reflowed or redispersed by stirring or shaking the container.
  • the cosmetic of the present disclosure contains the composition according to the first embodiment.
  • the cosmetic can contain a desired additive.
  • the cosmetic of the present disclosure has the same effect as the composition according to the first embodiment.
  • a method of manufacturing a composition and a cosmetic according to the present disclosure will be described.
  • the method described below is an example, and the manufacturing method is not limited to the following method. The above description is used for details of each component.
  • first addition step powder whose surface is charged with a first charge in a solvent is added to the solvent (first addition step). If necessary, the surface of the powder is charged (charging process). For example, the pH can be adjusted. Alternatively, the surface of the powder may be charged by adding a charge treatment agent to the solvent. For example, when it is desired to charge the powder surface positively, a cationic polymer such as polyethyleneimine can be added.
  • a polymer electrolyte that generates an ionic polymer having a second charge is added to the solvent (second addition step).
  • the ionic polymer generated by the ionization of the polymer electrolyte is electrically adsorbed on the surface of the powder.
  • the order of adding the powder and the polymer electrolyte is preferably such that the powder is added first.
  • the ionic polymer By adding the ionic polymer in the state where the powder is first dispersed, the ionic polymer can be easily adsorbed to the powder.
  • a treatment for relaxing the shrinkage of the polymer chain of the ionic polymer may be performed (relaxation step). For example, stress or strain such as pressure is applied to the liquid to entangle the polymer chains so that the polymer chains can extend outward from the adsorbed particles.
  • the application time of the pressure to the liquid is preferably 1 hour or longer in order to sufficiently relax the polymer chain.
  • the shrinkage of the polymer chain can be alleviated by sealing the container containing the liquid.
  • a compound for example, a salt that generates multivalent ions having the first charge, for example, by ionization is added to the mixture (third addition step).
  • the polyvalent ions generated in the solvent are ionic and / or electrostatically or weakly bound to the ionic polymers.
  • the powder is softly aggregated through the ionic polymer and the multivalent ions.
  • the addition rate of each component can be determined according to the content rate described above.
  • the composition and cosmetic of the present disclosure can be easily produced.
  • the powder, the ionic polymer and the multivalent ion are added simultaneously, it is considered that the polymer chain of the ionic polymer adsorbed on the powder contracts. For this reason, multivalent ions cannot connect ionic polymers to each other, and as a result, do not form a network, and the powder cannot form soft aggregates.
  • the polymer chain of the ionic polymer adsorbed on the powder can be extended. For this reason, multivalent ions link ionic polymers to each other, thereby forming a network, and the powder can form soft aggregates.
  • the composition of the present disclosure will be described below with examples. However, the composition of the present disclosure is not limited to the following examples.
  • the content of the ionic polymer shown in each table is the addition rate of the polymer electrolyte that is the basis of the ionic polymer.
  • the content rate of the multivalent ion shown in each table is the addition rate of the salt serving as the basis of the multivalent ion.
  • Test Example 1 Test Examples 1-1 to 1-6
  • Test Example 2 Test Examples 2-1 to 2-6
  • Test Example 3 Test Examples 3-1 to 3-6
  • Tables 1 to 3 show the compositions of the prepared compositions and the evaluation of dispersibility and redispersibility.
  • Water was used as a solvent.
  • zinc oxide powder having an average particle size of 0.05 ⁇ m (catalog value) was added to water.
  • the surface of the zinc oxide particles is considered to be positively charged in water.
  • ammonium polyacrylate which is a polymer electrolyte, was added to water, and ultrasonic vibration was applied to the mixture to disperse the zinc oxide powder.
  • Ammonium polyacrylate is ionized in water, and the produced ionic polymer is a polyacrylate ion having a carboxylate anion group having a negative charge.
  • the addition rate of “polymer electrolyte (ionic polymer)” shown in Tables 1 to 3 is the mass of polymer electrolyte per 1 g of powder.
  • magnesium chloride was added to the mixture as an electrolyte (salt) to be multivalent ions and mixed.
  • the addition rate of “salt (multivalent ion)” shown in Tables 1 to 3 is the mass of the electrolyte (salt) per 1 g of the polymer electrolyte.
  • FIG. 2 shows photographs of the composition immediately after the preparation and one day after the preparation in each test example.
  • the dispersibility was visually evaluated according to the following criteria.
  • FIG. 3 shows a photograph of the sample one day after preparation in Test Examples 1-3, 2-3, and 3-3 when the container is shaken by hand.
  • the dispersed particles settled immediately after preparation under the condition that the Mg 2+ addition amount was 0.2 g / (g-polymer) or more. In particular, under the conditions of 30% by mass and 40% by mass of the powder, no clarified layer was formed even when the slurry settled.
  • the dispersion of the powder can be achieved by adding the ionic polymer and the polyvalent ions. It was found that the property and redispersibility can be improved.
  • the content of the salt from which the multivalent ions are based is at least 0.05 parts by mass or more, preferably 0.1 parts by mass or more, more preferably 0.15 parts by mass or more per 1 part by mass of the polymer electrolyte. It has been found that the reflowability and redispersibility of the powder can be increased.
  • Test Example 4 In order to quantitatively evaluate the fluidity of the composition of the present disclosure, each of Test Examples 1-1 to 1-6, Test Examples 2-1 to 2-6, and Test Examples 3-1 to 3-6 The rheological properties of this composition were measured with a cone plate rheometer. 4 to 6 show the relationship between the shear rate and the shear stress.
  • FIG. 4 is a graph relating to Test Examples 1-1 to 1-6.
  • FIG. 5 is a graph relating to Test Examples 2-1 to 2-6.
  • FIG. 6 is a graph relating to Test Examples 3-1 to 3-6.
  • each composition has a yield value.
  • yield value is meant the force required for the powder in the composition to start moving.
  • the powder in the composition having a salt (multivalent ion) content of 0.2 to 2 g / g-polymer cannot start moving unless it is applied about 1.5 Pa. From this, it is shown that the deposited layer of zinc oxide behaves in a solid state in the stationary state.
  • the powders in the compositions of Test Examples 1-3 to 1-6, 2-3 to 2-6, and 3-3 to 3-6 behave as solids when left standing, and behave as fluids when used. Indicated. In the case of a composition having a salt (multivalent ion) content of 0 to 0.1 g / g-polymer, the powder is considered not to form soft agglomeration.
  • composition and cosmetics of the present invention, and the production methods thereof have been described based on the above embodiments and examples, but are not limited to the above embodiments and examples, and are within the scope of the present invention.
  • various modifications, changes and improvements can be made to each disclosed element (including elements described in the claims, the specification, and the drawings).
  • various combinations, substitutions, or selections of the disclosed elements are possible within the scope of the claims of the present invention.
  • composition of the present disclosure can be applied to all products using a slurry.
  • the composition of the present disclosure can be applied to cosmetics, paints, inks, foods, and the like.

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Abstract

L'invention concerne une composition qui comprend un solvant, le solvant renfermant les éléments suivants : une poudre présentant une première charge sur sa surface ; un polymère ionique présentant une seconde charge, qui est opposée à la première charge ; et des ions polyvalents présentant la première charge. La poudre et le polymère ionique ont été liés électrostatiquement et/ou ioniquement. Le polymère ionique et les ions polyvalents ont été liés électrostatiquement et/ou ioniquement.
PCT/JP2018/001618 2017-01-23 2018-01-19 Composition contenant une poudre, procédé de production associé et préparation cosmétique Ceased WO2018135626A1 (fr)

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BR112019014612-1A BR112019014612A2 (pt) 2017-01-23 2018-01-19 Composição contendo pó, seu método de produção e preparação cosmética
EP18741641.7A EP3572467A4 (fr) 2017-01-23 2018-01-19 Composition contenant une poudre, procédé de production associé et préparation cosmétique
US16/477,659 US20190358131A1 (en) 2017-01-23 2018-01-19 Powder-containing composition, production method therefor, and cosmetic preparation
JP2018562453A JP6909240B2 (ja) 2017-01-23 2018-01-19 粉末含有組成物及びその製造方法、並びに化粧料
KR1020197020327A KR102241317B1 (ko) 2017-01-23 2018-01-19 분말 함유 조성물 및 그 제조 방법, 및 화장료
RU2019123826A RU2761628C2 (ru) 2017-01-23 2018-01-19 Композиция, содержащая порошок, способ ее получения и косметическое средство
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See also references of EP3572467A4

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RU2761628C2 (ru) 2021-12-13
CN110177842B (zh) 2021-11-05
EP3572467A4 (fr) 2020-09-02
CN110177842A (zh) 2019-08-27
RU2019123826A3 (fr) 2021-04-15
BR112019014612A2 (pt) 2020-02-27
EP3572467A1 (fr) 2019-11-27
KR102241317B1 (ko) 2021-04-15
KR20190096375A (ko) 2019-08-19
RU2019123826A (ru) 2021-02-24
TWI770109B (zh) 2022-07-11
JPWO2018135626A1 (ja) 2019-12-12
US20190358131A1 (en) 2019-11-28
TW201832752A (zh) 2018-09-16
JP6909240B2 (ja) 2021-07-28

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